75 First Dates, a Tinder Tour, and the Dating App Playbook That Actually Works (feat. Alex Jacobs)

This week Holly is joined by Alex Jacobs — NYC-based tutor, musician, the friend-of-her-best-friend she somehow went to Oberlin with for four years without ever meeting, and a certified, gold-medal, dating-app savant. Alex spent his 20s in New York in a string of serial monogamous relationships, drumming in indie bands, and at one point touring the country in a pop duo with a girl he matched with on Tinder. Then at 33 he was properly single for the first time in his life, went on 75 first dates, did actual research into the apps, and met his current girlfriend — on Tinder — by gaming the algorithm in ways he is now generously sharing with the rest of us.In this episode: the band era and Saturn return collapsing at once, the worst dates of his life (including the tiptoe-maxing incident), his dad's pre-internet pickup strategy, and the full dating app optimization framework. Photos, prompts, swiping, parameters, why you should never pay, the bottom-age-range hack — all of it. Find AlexInstagramSoundcloudFind NecterineInstagramTikTokSubstack